反応 #2267088

反応方程式

water

(rac)-2-[(8-iodo-2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-yl)methyl]-1H-isoindole-1,3(2H)-dione

2,4-dichlorophenylboronic acid

K2CO3

2,4-Dichlorophenylboronic acid

2,4-Dichlorophenylboronic acid

K2CO3

→

colorless solid

収率 32.9%

(rac)-2-{[8-(2,4-dichlorophenyl)-2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-yl]methyl}-1H-isoindole-1,3(2H)-dione

収率 32.9%

溶媒

EtOAc

THF DMA

反応条件

後処理

1. 1
   温度heat
2. 2
   温度heat
3. 3
   workup.WAITwas continued for another 3 h
4. 4
   温度After cooling down to rt
5. 5
   その他separated
6. 6
   抽出The aqueous layer was extracted with EtOAc (2×)
7. 7
   乾燥The combined EtOAc solution was dried over MgSO4
8. 8
   ろ過filtered
9. 9
   濃縮The filtrate was concentrated in vacuo to dryness

実験手順

A mixture of (rac)-2-[(8-iodo-2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-yl)methyl]-1H-isoindole-1,3(2H)-dione (0.044 g, 0.098 mmol), 2,4-dichlorophenylboronic acid (0.028 g, 0.147 mmol), tetrakis(triphenylphosphine)palladium (0.011 g, 0.01 mmol) and K2CO3 (0.054 g, 0.39 mmol) in THF-DMA (1:1, 2.0 mL) was heated at 66° C. for 2 h. 2,4-Dichlorophenylboronic acid (0.02 g, 0.105 mmol), tetrakis(triphenyl-phosphine)palladium (0.007 g, 0.006 mmol) and K2CO3 (0.02 g, 0.145 mmol) were added and heat was continued for 24 h. 2,4-Dichlorophenylboronic acid (0.02 g, 0.105 mmol) and tetrakis(triphenyl-phosphine)palladium (0.007 g, 0.006 mmol) were again added and heat was continued for another 3 h. After cooling down to rt, water (10.0 mL) and EtOAc (10.0 mL) were added and separated. The aqueous layer was extracted with EtOAc (2×). The combined EtOAc solution was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to prep TLC (EtOAc/hexane, 1:2) to give 0.015 g (32%) of colorless solid as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.92-7.90 (m, 2 H), 7.81-7.78 (m, 2 H), 7.45 (d, J=2.0 Hz, 1 H), 7.27-7.18 (m, 2 H), 6.80 (s, 1 H), 6.74 (s, 1 H), 4.51-4.47 (m, 2 H), 4.13-4.09 (m, 1 H), 4.03-3.97 (m, 1 H), 3.83-3.79 (m, 1 H), 3.46-3.42 (m, 1 H), 3.38-3.35 (m, 1 H), 3.23-3.19 (m, 1 H), 3.16-3.14 (m, 1 H).

出典